Formaldehyde → HCID 54698243, compound

HRID 2214645Notes

Reaction equation

HRID 2214645 reaction equation
CO[C:3](=[O:26])[C:4]([OH:25])=[CH:5][C:6](=[O:24])[N:7]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.C=O.CN.ClC1C=C(C=CC=1Cl)[CH2:35][N:36](C)[C:37](C1CN(C)C(=O)C=1O)=O>>[Cl:23][C:18]1[CH:17]=[C:16]([N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:6]([C:5]2[CH2:35][N:36]([CH3:37])[C:3](=[O:26])[C:4]=2[OH:25])=[O:24])[CH:21]=[CH:20][C:19]=1[Cl:22]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6329MethylamineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655724HCID 69655724, compound2×

Product 1

HCID 54698243HCID 54698243, compoundYield 68%

Procedure

3-[(3,4-Dichlorophenyl)-(4-fluorobenzyl)-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 78-B) was treated with paraformaldehyde and methylamine as described in the preparation of Compound 12 to give the title compound as a white solid (68% yield); mp 195° C., dec. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.9 (3H, s, NCH3), 3.03 (2H, s, NCH2), 4.90 (2H, s, NCH2), 6.87 (1H, dd, J=2.5 Hz and J=8.6 Hz, aromatic), 7.02 (2H, m, aromatics), 7.2 (2H, m, aromatics), 7.22 (1H, d, J=2.5 Hz, aromatic), 7.49 (1H, d, J=8.6 Hz, aromatic), 11.9 (1H, broad, OH). Anal. calcd for C19H15Cl2FN2O3: C, 55.76; H, 3.69; N, 6.84. Found: C, 55.53; H, 3.61; N, 6.75.

Sources & evidence

ORD record
ord-b1e38f4490ea4055bd155730be6a6e3d
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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